(1R,2S)-N-tert-Butoxycarbonyl-3-tert-butyldimethylsilyloxy-2-hydroxy-1-phenyl-1-propylamine → (2S,3R)-3-amino-3-phenylpropane-1,2-diol hydrochloride

HRID 64457Notes

Reaction equation

HRID 64457 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C@H:9]([OH:19])[CH2:10][O:11][Si](C(C)(C)C)(C)C)(C)(C)C.[ClH:27].O1CCOCC1>CO>[ClH:27].[NH2:7][C@H:8]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C@H:9]([OH:19])[CH2:10][OH:11]

Participants

4

Reactant 2

HCID 15408403(1R,2S)-N-tert-Butoxycarbonyl-3-tert-butyldimethylsilyloxy-2-hydroxy-1-phenyl-1-propylamineHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 86713470(2S,3R)-3-amino-3-phenylpropane-1,2-diol hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 300 mg of tert-butyl[(1R,2S)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-hydroxy-1-phenylpropyl]carbamate and 5 ml of methanol was added 5 ml of a 4 M hydrogen chloride/dioxane solution, followed by stirring for 2 hours. The solvent was evaporated under reduced pressure to obtain 171 mg of (2S,3R)-3-amino-3-phenylpropane-1,2-diol hydrochloride.

Workup

  1. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-02ac9ca8e20e4514a3a3eb9802c66746
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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